Abstract Approximately 23% of Americans take 3 or more prescription medications, often as a part of complex drug regimens that challenge adherence, contributing to treatment failures and costing US healthcare $100 billion or more, annually. Difficulties managing polypharmacy negatively impact all stakeholders ? patients, doctors, pharmacies and insurers. The problem is particularly significant in elder-care, as the likelihood of developing chronic conditions treatable by medication increases and multiple characteristics of this population pose assorted risks for medication errors. Custom multimedication packaging has shown promise in addressing some of the drivers of non-adherence, but offers no solution for other drivers such as errors in drug reconciliation, healthcare practitioner involvement, care coordination and patient education. The multiple stakeholders in medication prescribing and utilization practices constitute a variety of potential sources of medication management problems, but also a diverse set of clients for polypharmacy solutions. Insightfil is developing a comprehensive medication management solution that incorporates convenience packaging with passive detection of medication adherence to provide essential and medicine-related information in real-time generating a channel for more accurate information exchange between all stakeholders for improved patient care and satisfaction. In previous work, we designed, built and tested a robotic workstation that offers innovative patient drug packaging, which is unique in its ability to avoid medication cross-contamination. Leveraging our successful launch of the medication dispensing robot, the goal of this Phase I SBIR is to develop instrument pill pouches and use the resulting real- time adherence data to improve the way patients are nudged into increased adherence through more personalized and context-specific communications. Toward this end we propose Specific Aims to develop three components of the technology: 1) a near-field communication (NFC) sensor that is compatible with the emerging industry standard for custom fill convenience packaging; 2) a smartphone app that reads the NFC tags to verify that a medication pack has been opened; and 3) a smartphone app to deliver real-time, context sensitive patient messaging based on medication use patterns. Once the prototype system is developed, we will conduct a pilot study (Specific Aim 4) of 30 multimedication users to provide preliminary evidence of the efficacy and acceptability of Insightfil's platform technology. After establishing proof-of-concept through the completion of the SBIR Phase I project, we will refine the resulting prototype technology into a more robust commercial grade system with an expanded-features patient app ready for pilot deployment in 1-2 pharmacies serving 5,000 patients (Phase II). Significantly, the research design required for commercialization will not require FDA approval for deployment in pharmacies - Pharmacists will follow all regulations applicable to the dispensing of medications.